(S)-N-(1-phenylpropyl)-2-phenyl-3-{[(trifluoromethyl)sulfonyl]oxy}quinoline-4-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (S)-N-(1-phenylpropyl)-2-phenyl-3-{[(trifluoromethyl)sulfonyl]oxy}quinoline-4-carboxamide
• 英文别名: trifluoro-methanesulfonic acid 2-phenyl-4-((S)-1-phenyl-propylcarbamoyl)-quinolin-3-yl ester；[2-phenyl-4-[[(1S)-1-phenylpropyl]carbamoyl]quinolin-3-yl] trifluoromethanesulfonate
• 化学式: C₂₆H₂₁F₃N₂O₄S
• 分子量: 514.525
• InChiKey: VRRJAJRQBMCIIO-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-[N,正双(三氟甲烷烷磺酰)氨基]-5-氯吡啶 、 (-)-(S)-N-(alpha-乙基苄基)-3-羟基-2-苯基喹啉-4-羧酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到(S)-N-(1-phenylpropyl)-2-phenyl-3-{[(trifluoromethyl)sulfonyl]oxy}quinoline-4-carboxamide
  参考文献：
  名称：

  Functionalization through Lithiation of (S)-N-(1-Phenylpropyl)-2-phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200

  摘要：

  Lithiation of (S)-N-(1-phenylpropyl)-2-phenylquinoline-4-carboxamide with the complex n-BuLi/TMEDA (1/1 molar ratio) in THF at -60 degrees C for 5 h occurred selectively at the position 3 of the quinoline ring. This selectivity was shown by the absence of racemization of the stereogenic center and the formation of the corresponding functionalized quinolines in 59-74% yield by subsequent reaction with an electrophile at -60 degrees C for 1 h. The 3-trimethylstannyl derivative was subjected to a Stille reaction using methyl, phenyl, or thienyliodide to afford the alkyl or aryl quinolines in moderate to good yields. This methodology was successfully applied to the radiosynthesis of [C-11] SB 222200 using methyl iodide labeled with carbon-11 (beta(+) emitter, t(1/2) = 20.4 min) for the in vivo study of NK-3 receptor by positron emission tomography (48-58% radiochemical yields from [C-11] CH3I, decay corrected, 45 min total synthesis time).

  DOI：

  10.1021/jo062285p

文献信息

• QUINOLINE 3 -SULFONATE ESTERS AS NK3 RECEPTOR MODULATORS
  申请人：AstraZeneca AB

  公开号：EP1896418A1

  公开（公告）日：2008-03-12
• Quinoline 3-Sulfonate Esters as Nk3 Receptor Modulators
  申请人：Simpson Thomas R.

  公开号：US20080194622A1

  公开（公告）日：2008-08-14

  Compounds of Formula I wherein R 1 , A, R 2 , R 3 , R 4 , R 5 n, m and q are as described in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.
• [EN] Quinoline 3 -sulfonate esters as NK3 receptor modulators<br/>[FR] ESTERS DE QUINOLINE-3-SULFONATE EN TANT QUE RÉGULATEURS DE RÉCEPTEURS NK3
  申请人：ASTRAZENECA

  公开号：WO2006137789A1

  公开（公告）日：2006-12-28

  [EN] Compounds of Formula I wherein R¹, A, R², R³, R⁴, R⁵ n, m and q are as described in the specification, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.
  [FR] La présente invention décrit des composés de Formule I où R¹, A, R², R³, R⁴, R⁵, n, m et q sont tels que définis dans la description de l'invention, des sels de qualité pharmaceutique, des méthodes de fabrication, des préparations pharmaceutiques contenant lesdits composés ainsi que leurs méthodes d'utilisation.
• Functionalization through Lithiation of (<i>S</i>)-<i>N</i>-(1-Phenylpropyl)-2-phenylquinoline-4-carboxamide. Application to the Labeling with Carbon-11 of NK-3 Receptor Antagonist SB 222200
  作者：Idriss Bennacef、Cécile Perrio、Marie-Claire Lasne、Louisa Barré

  DOI：10.1021/jo062285p

  日期：2007.3.1

  Lithiation of (S)-N-(1-phenylpropyl)-2-phenylquinoline-4-carboxamide with the complex n-BuLi/TMEDA (1/1 molar ratio) in THF at -60 degrees C for 5 h occurred selectively at the position 3 of the quinoline ring. This selectivity was shown by the absence of racemization of the stereogenic center and the formation of the corresponding functionalized quinolines in 59-74% yield by subsequent reaction with an electrophile at -60 degrees C for 1 h. The 3-trimethylstannyl derivative was subjected to a Stille reaction using methyl, phenyl, or thienyliodide to afford the alkyl or aryl quinolines in moderate to good yields. This methodology was successfully applied to the radiosynthesis of [C-11] SB 222200 using methyl iodide labeled with carbon-11 (beta(+) emitter, t(1/2) = 20.4 min) for the in vivo study of NK-3 receptor by positron emission tomography (48-58% radiochemical yields from [C-11] CH3I, decay corrected, 45 min total synthesis time).